Ethyl chloroformate → HCID 66914791, compound

HRID 880456Notes

Reaction equation

HRID 880456 reaction equation
C([Li])CCC.[CH3:6][C:7]1[NH:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:11]=1.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>O1CCCC1>[CH3:6][C:7]1[N:8]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:9]=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 12303555HCID 12303555, compoundHCID 178418339Butyllithium

Product 1

HCID 66914791HCID 66914791, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (0.87 mL, 1.6M solution, 1.40 mmol) was added to a cold (below 0° C.) solution of 2-methyl-4-phenyl-1H-pyrrole (200 mg, 1.27 mmol) in tetrahydrofuran (6 mL) and stirred at below 0° C. for 20 min. Ethyl chloroformate (0.1 mL, 1.02 mmol) was added slowly to the reaction mixture and stirred at 0 to 10° C. for 90 min. The reaction mixture was quenched into saturated ammonium chloride solution and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, brine, dried over anhydrous sodium sulphate and concentrated in vacuo to afford ethyl 2-methyl-4-phenyl-pyrrole-1-carboxylate (250 mg, 86%) as a brown solid.

Workup

  1. stirringstirred at 0 to 10° C. for 90 min
  2. customThe reaction mixture was quenched into saturated ammonium chloride solution
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium bicarbonate solution, brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-944830d816ff4889808f705959cb6caf
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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